
Herbie Hancock, the 86-year-old jazz keyboardist, plays Toronto’s Massey Hall on July 26.Supplied
With Herbie Hancock’s illustrious history as a bandleader, it’s hard to think of the jazz icon as a disciple. But in 1963, after the release of his debut album, Takin’ Off (which included the hit single Watermelon Man), a young Hancock joined Miles Davis’s quintet and for five years was something of a mentee.
The 86-year-old keyboardist, who plays Toronto’s Massey Hall on July 26, spoke from his home in Los Angeles about working with Davis − the jazz god, and the teacher.
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You joined Miles Davis’s group with bassist Ron Carter and drummer Tony Williams. Was Davis a mentor? Did he champion you guys? Or was he simply interested in putting together the best band he could?
All the above. He didn’t talk much on the bandstand. But sometimes he would tell us stories about working with Charlie Parker and other musicians. It was always great when Miles was in a talkative mood.
In what form did his mentorship take shape?
He cared about us. I actually never dreamed of playing with him. He was in the heavens, one of the gods. It was a few months before I realized Miles was listening to me when he played his solos. I thought I was in the background. I didn’t want to get in the way of anything he was trying to play. And if you listen to some of the records I did with him, it sounded like that.
Was there a moment where you realized he was hearing you?
We were playing at the Village Vanguard in New York. I noticed Miles, during one of his solos, shifted his notes to work with the chord I had played. That was surprising to me. When I listened more closely, I realized he was listening to us all. Ron Carter, on his bass lines, would go down. Miles would go up. Same with Tony Williams. So, yes, Miles was listening.
Isn’t there a story about you making a mistake during a concert and Miles went along with it?
Yes, in Europe, in 1963, I think. It was on the song So What. At that point in the show, it was the best concert we’d done on the tour. People were on the edge of their seats. I played the wrong chord, and I felt like I had destroyed everything we’d done that night. But Miles played these notes that made my chord fit.
How did it feel in the moment?
I couldn’t really play anything after it happened. I was so shocked. We finished the show, but I was wondering, ‘Is he Merlin the Magician? How did he do that?’

Hancock in 2007.Kwaku Alston/Supplied
Was there a point when you consciously began helping younger artists? I’m thinking about Wynton Marsalis in the early eighties.
When I hired Wynton to tour with Tony, Ron and me, I wasn’t thinking that way. I received a call from Columbia Records. They said they had this young trumpet player they were considering recording. They wanted me to produce the record and sent me a couple of his recordings. One of them was a double trumpet concerto he played with his trumpet teacher and an orchestra in New Orleans. It sounded fantastic.
Were Tony and Ron on board?
I had to convince them [laughs]. I needed their okay. I said, ‘Look, maybe it’s a chance to welcome the next generation of musicians.’ Tony was young himself. They finally agreed, reluctantly. There was a tendency with Ron and Tony to feel like the connection with the three of us was our own thing. To work with Wayne Shorter or Freddie Hubbard, that was cool. But to let in somebody who was brand new, they weren’t excited about doing that.
Did you audition Wynton?
I think we had a couple of rehearsals. It worked out well enough that Ron and Tony agreed to do the tour, which went really well. We were in Japan when Wynton called his brother [saxophonist Branford Marsalis] and asked him to come over. That’s where I met him.
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Your classic instrumental Watermelon Man was successful commercially, particularly Mongo Santamaría‘s version in 1963. You recorded it more than once yourself. How would you record it today?
That’s a good question. I can’t answer that.
Would you hire someone to rap over it? Would you arrange and produce it differently today, to allow for contemporary tastes?
Not necessarily. I’m very used to doing things a different way, other than what’s expected. I don’t let convention direct my approach.
Clive Davis, who died recently, signed you to Columbia Records in the 1970s. Did you go to his funeral?
No, I did not. But, yes, he signed me to Columbia. I didn’t have a strong relationship with him directly at that time. But I was invited to his Grammy parties since. He was a fun guy to be around.
Last question. You received the Kennedy Center Honor in 2013. What are your thoughts on what has happened to the Kennedy Center under the current Trump administration?
I think Trump is losing fans, and I’m happy about that. The things he’s said about the Obama family are atrocious. But, in a sense, I pity him. He’s a sick man. I think it’s difficult for him to have any understanding of what happiness is all about.
Can the Kennedy Center recover after Trump is gone?
I’m not the one to answer that one. We can only see.
This interview has been edited and condensed.